Boron tribromide → (R)-1-[5-(4-chlorophenoxy)pyrazin-2-yl]-5-(3-hydroxyphenyl)pyrrolidin-2-one

HRID 1972246노트

반응식

HRID 1972246 반응식
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[N:8]=[CH:9][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([O:24]C)[CH:19]=4)[CH2:16][CH2:15][C:14]3=[O:26])=[N:11][CH:12]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[N:8]=[CH:9][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=4)[CH2:16][CH2:15][C:14]3=[O:26])=[N:11][CH:12]=2)=[CH:27][CH:28]=1

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 59485648(R)-1-[5-(4-chlorophenoxy)pyrazin-2-yl]-5-(3-methoxyphenyl)pyrrolidin-2-one

생성물 1

HCID 59485583(R)-1-[5-(4-chlorophenoxy)pyrazin-2-yl]-5-(3-hydroxyphenyl)pyrrolidin-2-one수율 100.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A mixture of (R)-1-[5-(4-chlorophenoxy)pyrazin-2-yl]-5-(3-methoxyphenyl)pyrrolidin-2-one (286 mg, 0.72 mmol), DCM (10 mL) and BBr3 (1M in DCM, 4 mL) is stirred at room temperature for 1 h. The reaction mixture is then diluted with DCM (120 mL), washed with saturated NaHCO3 (20 mL) and brine (20 mL) and dried over Na2SO4. After concentrating, the residue is purified on silica gel (0-33% ethyl acetate in hexane) to give (R)-1-[5-(4-chlorophenoxy)pyrazin-2-yl]-5-(3-hydroxyphenyl)pyrrolidin-2-one (276 mg, 100%) as a white solid. HPLC-MS calculated for C20H16ClN3O3 (M+H+) 382.09, found 382.10.

후처리

  1. washwashed with saturated NaHCO3 (20 mL) and brine (20 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationAfter concentrating
  4. customthe residue is purified on silica gel (0-33% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-3ced979531644e578809dc8338355e15
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431607B2

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